Potassium Hydroxide → 1-Phenylcyclopropanecarboxylic acid

HRID 2042903Notes

Reaction equation

HRID 2042903 reaction equation
[C:1]1([C:7]2([C:10]#N)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-:12].[K+].[OH-:14].[Na+]>C(O)C>[C:1]1([C:7]2([C:10]([OH:14])=[O:12])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 702881-Phenylcyclopropanecarbonitrile

Product 1

HCID 802061-Phenylcyclopropanecarboxylic acidYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The phenylcyclopropanecarboxylic acid 43 used as a intermediate in preparing the thiazole containing C-aryl glucoside can be prepared by a method as shown in Scheme 8. The phenylacetonitrile β-39 is reacted with 1,2-dibromoethane in the presence of sodium hydroxide and a phase-transfer catalyst in toluene and water to provide a corresponding phenylcyclopropanecarbonitrile 42 in 71% yield. This carbonitrile 42 is treated with potassium hydroxide and sodium hydroxide in refluxed aqueous ethanol to provide cyclopropanecarboxylic acid 43 in 95% yield.

Sources & evidence

ORD record
ord-98154ee986064f3596eb32fa039c056b
Source dataset
uspto-grants-2013_11
Patent number
US08586550B2

Reaction notes

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